MXPA97002479A - Photostable filtering composition comprising a derivative of dibenzoylmethane and a polyacaride alkileter and its utilization - Google Patents
Photostable filtering composition comprising a derivative of dibenzoylmethane and a polyacaride alkileter and its utilizationInfo
- Publication number
- MXPA97002479A MXPA97002479A MXPA/A/1997/002479A MX9702479A MXPA97002479A MX PA97002479 A MXPA97002479 A MX PA97002479A MX 9702479 A MX9702479 A MX 9702479A MX PA97002479 A MXPA97002479 A MX PA97002479A
- Authority
- MX
- Mexico
- Prior art keywords
- tert
- butyl
- composition
- methoxydibenzoylmethane
- dibenzoylmethane
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 82
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 title claims description 41
- 238000001914 filtration Methods 0.000 title description 7
- -1 dibenzoylmethane compound Chemical class 0.000 claims abstract description 29
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 29
- 239000005017 polysaccharide Substances 0.000 claims abstract description 29
- 239000002537 cosmetic Substances 0.000 claims abstract description 12
- 150000005215 alkyl ethers Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 230000005855 radiation Effects 0.000 claims description 18
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 17
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 210000004209 hair Anatomy 0.000 claims description 9
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 claims description 8
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229930182830 galactose Natural products 0.000 claims description 8
- 230000004224 protection Effects 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229920002907 Guar gum Polymers 0.000 claims description 6
- 239000000665 guar gum Substances 0.000 claims description 6
- 235000010417 guar gum Nutrition 0.000 claims description 6
- 229960002154 guar gum Drugs 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 5
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims description 5
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 5
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 5
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 5
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 244000303965 Cyamopsis psoralioides Species 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 229920000569 Gum karaya Polymers 0.000 claims description 4
- 229920000161 Locust bean gum Polymers 0.000 claims description 4
- 241000934878 Sterculia Species 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- 150000002243 furanoses Chemical class 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 239000000231 karaya gum Substances 0.000 claims description 4
- 235000010494 karaya gum Nutrition 0.000 claims description 4
- 229940039371 karaya gum Drugs 0.000 claims description 4
- 239000000711 locust bean gum Substances 0.000 claims description 4
- 235000010420 locust bean gum Nutrition 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- 229920000591 gum Polymers 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 150000004676 glycans Chemical class 0.000 abstract description 4
- 230000003711 photoprotective effect Effects 0.000 abstract description 2
- 125000001483 monosaccharide substituent group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 11
- 210000003491 skin Anatomy 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 5
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- 239000003795 chemical substances by application Substances 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000000475 sunscreen effect Effects 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 2
- 230000003113 alkalizing effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 208000017983 photosensitivity disease Diseases 0.000 description 2
- 231100000434 photosensitization Toxicity 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- RMFFCSRJWUBPBJ-UHFFFAOYSA-N 15-hydroxypentadecyl benzoate Chemical compound OCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 RMFFCSRJWUBPBJ-UHFFFAOYSA-N 0.000 description 1
- UIVPNOBLHXUKDX-UHFFFAOYSA-N 3,5,5-trimethylhexyl 3,5,5-trimethylhexanoate Chemical compound CC(C)(C)CC(C)CCOC(=O)CC(C)CC(C)(C)C UIVPNOBLHXUKDX-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
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- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 210000000720 eyelash Anatomy 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
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- 235000013336 milk Nutrition 0.000 description 1
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- 210000004080 milk Anatomy 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
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Abstract
The present invention relates to a stable photoprotective cosmetic / dermatological composition characterized in that it comprises: a) an effective amount of at least one dibenzoylmethane compound, and b) an effective photostabilising amount of at least one alkyl ether of polysaccharide, wherein at least one polysaccharide alkyl ether comprises structural units containing at least two different monosaccharide ring members, each unit comprising at least one radical substituent
Description
PHOTOSTABLE FILTERING COMPOSITION COMPRISING A DERIVATIVE OF DIBENZOYLMETHANE AND A POLYACARIDE ALKYLENE AND ITS
UTILIZATIONS
FIELD OF INVENTION
The present invention relates, among other objects, to new cosmetic and / or dermatological compositions intended for the photoprotection of the skin and / or of the hair against ultraviolet radiation (compositions hereinafter more simply referred to as filtering compositions), when used in the aforementioned cosmetic application, as well as to a general method of photosensitization of particular sunscreens, active to UV-A rays, by means of a particular polyacrylate alkyl ether, more precisely still, the invention relates to filtering compositions photo-stable with respect to UV rays comprising, on a cosmetically and / or dermatologically acceptable support, at least one compound selected from the dibenzoylmethane derivatives as an organic sunscreen active at UV-A, associated with this particular alkylcarbamate polysaccharide. photo stabilizing agent, as well as the procedure corresponding stabilization of the dibenzoylmethane derivative by means of this polysaccharide alkyl ether.
REF: 24484 BACKGROUND OF THE INVENTION
It is known that light radiations of wavelengths comprised between 280 nm and 400 n allow tanning of the human epidermis and that rays with wavelengths between 280 nm and 320 nm, known under the name of UV-B, cause erythema and skin burns that can impair the development of natural tanning; this UV-B radiation must therefore be filtered. It is also known that UV-A rays, with wavelengths comprised between 320 nm and 400 nm, which cause tanning of the skin, are capable of inducing an alteration thereof, particularly in the case of sensitive skin or skin. of a skin continually exposed to solar radiation. UV-A rays cause, in particular, a loss of elasticity of the skin and the appearance of wrinkles that lead to premature aging. They favor the triggering of the erythematous reaction or amplify this reaction in some subjects and may even be the origin of phototoxic or photoallergic reactions. It is therefore desirable to also filter the UV-A radiation. In this respect, a particularly interesting family of UV-A filters is currently constituted by the dibenzoylmethane derivatives, and particularly 4- (tert-butyl) 4'-methoxy dibenzoylmethane, which in fact have a strong intrinsic absorption power. These dibenzoylmethane derivatives, which are now well-known products by themselves as UV-A active filters, are described in particular in the French patent applications FR-A-2,326,405 and FR-A-2,440,933, as well as in the European patent application EP-A-0114607; 4- (tert-butyl) 4'-methoxy dibenzoylmethane is on the other hand currently proposed for sale under the trade name of "PARSOL 1789" by the company GIVAUDAN. Unfortunately, it is observed that dibenzoylmethane derivatives are products that are relatively sensitive to ultraviolet radiation (especially to UV-A rays), that is, more precisely, that present an annoying tendency to degrade more or less rapidly under the action of this latest. Thus, this substantial lack of photochemical stability of the dibenzoylmethane derivatives against the ultraviolet radiation to which they are naturally intended to be subjected does not guarantee constant protection during prolonged exposure to the sun, so that applications repeated at intervals of Regular and close time must be performed by the user to obtain an effective protection of the skin against UV radiation, which is annoying for the user.
The photosensitization of dibenzoylmethane derivatives with respect to UV radiation is, today, a problem that has not yet been solved in a completely satisfactory manner.
BRIEF DESCRIPTION OF THE INVENTION
Now, the Applicant has now discovered, unexpectedly and surprisingly, that by associating the aforementioned dibenzoylmethane derivatives with an effective amount of at least one particular polysaccharide alkyl ether, it was possible to substantially improve and. remarkable, the photochemical stability (or photostability) of these same derivatives of dibenzoylmethane. This discovery forms the basis of the present invention. Thus, according to a first object of the present invention, new compositions are proposed, more particularly intended for the protection of the skin and / or hair against ultraviolet radiation, of the type that they particularly comprise in a cosmetically acceptable support, at least a derivative of dibenzoylmethane, characterized in that they also comprise at least one polysaccharide alkyl ether formed by units including at least two different osidic rings, each ring including at least one hydroxyl group substituted by a saturated hydrocarbon alkyl chain. The compositions according to the invention have the advantage of being particularly photostable, even after prolonged exposure to UV-A and UV-B radiation. This radiation can be of natural origin (sun) or artificial (UV lamp). The subject of the present invention is also a novel process for stabilizing the dibenzoylmethane derivatives with respect to UV radiation, consisting of associating with the said dibenzoylmethane derivatives an effective amount of at least one alkyl ether of polysaccharide. formed by units that include at least two different osidic rings, each unit including at least one hydroxyl group substituted by a saturated hydrocarbon alkyl chain. The subject of the present invention is also the use of a polysaccharide alkyl ether formed by motifs that include at least two different osidic rings, each motif including at least one hydroxyl group substituted by a saturated hydrocarbon alkyl chain, to stabilize a UV-ray derivative of dibenzoylmethane contained in a filter cosmetic composition.
Still another object of the present invention resides in a method of cosmetic treatment for the protection of the skin and / or hair against ultraviolet radiation, consisting in applying to the latter an effective amount of a conformable photostable composition of the invention. Other features, aspects and advantages of the present invention will appear on reading the detailed description that follows.
DETAILED DESCRIPTION OF THE INVENTION
As indicated above, the dibenzoylmethane derivatives intended to be photostabilized according to the present invention are already well known products and are described in particular in documents FR-A-2,326,405, FR-A-2,440,933 and EP- A-0114.607 previously cited. According to the present invention, it is well understood to use one or more derivatives of dibenzoylmethane. Among the dibenzoylmethane derivatives which can be used according to the present invention, mention may be made in particular of, but not limited to: 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane and 2,4-dimethyldibenzoylmethane on 2; 5-dimethyldibenzoylmethane 4,4'-diisopropyldibenzoylmethane 4-tert-butyl-4'-methoxydibenzoylmethane 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane 2-methyl-5-tert-butyl-4'-methoxydibenzoylmethane 2 , 4-dimethyl-4'-methoxydibenzoylmethane, 2, β-dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane. Among the dibenzoylmethane derivatives mentioned above, it is very particularly preferred, according to the present invention, to use 4- (tert-butyl) -4'-methoxy dibenzoylmethane, particularly that proposed for sale under the trade name "PARSOL 1789" by the Society GIVAUDAN, answering this filter then to the following developed formula:
Another preferred dibenzoylmethane derivative according to the present invention is 4-isopropyl-dibenzoylmethane, a filter sold under the name "EUSOLEX 8020" by the company MERCK, and which corresponds to the following developed formula:
The dibenzoylmethane derivative (s) can be present in the compositions according to the invention, or in the compositions intended according to the process of the invention, with contents generally ranging between 0.01% and 10% by weight, and preferably with contents that range between 0.3% and 5% by weight, in relation to the total weight of the composition. According to a particular embodiment of the invention, the polysaccharide alkyl ether has a molecular weight greater than 100,000, and preferably greater than 200,000. Each unit may comprise from one to six and preferably from two to four hydroxyl groups substituted by one. saturated hydrocarbon alkyl chain. By saturated hydrocarbon alkyl chain, is meant a chain including from 1 to 24, preferably from 1 to 10 and better from 1 to 5 carbon atoms. In particular, the alkyl chain is chosen from the methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl chains. Osidic cycles are particularly chosen among mannose, galactose, glucose, furanose, rhamnose, arabinose. According to a preferred embodiment of the invention, the polysaccharide alkyl ether according to the invention is an alkyl ether of a gum and more particularly of a globally non-ionic gum, that is to say practically without an ionic group. Suitable gums include, for example, guar gum whose unit comprises a galactose and a gum. Maas, carob gum whose unit comprises a galactose and a mannose, karaya gum which is a complex mixture of rhamnose, galactose and galacturonic acid, the gum that is a complex mixture of arabinose, galactose and galacturonic acid. According to a preferred embodiment of the invention, the polysaccharide alkyl ether is a derivative of guar gum, and more particularly guarethylated with a degree of substitution of about 2 to 3, in particular 2.5, as described in the document RD 95378007 (October 1995). The effective amount of polysaccharide alkyl ether according to the invention is understood as an amount sufficient to obtain a significant and significant improvement in the photostability of the dibenzoylmethane derivative (s) contained in the composition. The minimum amount of stabilizing agent to be used, which can vary according to the nature of the cosmetically acceptable support retained for the composition, can be determined without any difficulty by means of a classic photostability measurement assay, such as that given in the examples given below . The compositions according to the invention may contain, for example, an amount of alkyl ether of polysaccharide according to the invention ranging from 0.5 to 20%, and preferably between 2 and 10% of the total weight of the composition. The photostable filtering cosmetic compositions according to the invention can be understood to contain, in addition to the dibenzoylmethane derivatives, one or more complementary sunscreens active at UVA and / or UVB, hydrophilic or lipophilic. The presence of complementary active filters to UV-B rays (wavelengths comprised between 280 nm and 320 nm approximately) thus makes it possible to have final compositions capable of filtering the whole of UV rays. The compositions of the invention may also comprise conventional cosmetic and / or dermatological adjuvants particularly selected from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, opacifiers, stabilizers, emollients, silicones. , a-hydroxy acids, anti-foam agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, fillers, pigments (mineral or organic), sequestrants, polymers, propellants, alkalizing agents, polymers, propellants, alkalizing or acidulating agents, dyes, or any other ingredient commonly used in cosmetics, in particular for the manufacture of filter compositions. All right, all. Supplementary ingredients susceptible to be introduced into the compositions according to the invention must be such as not to disturb or substantially alter the photostabilization effect exerted by the polysaccharide alkyl ether according to the invention on the dibenzoylmethane derivatives. The fatty substances can be constituted by an oil or a wax or its mixtures; they also include fatty acids, fatty alcohols and fatty acid esters. The oils can be chosen from animal, vegetable, mineral or synthetic oils and particularly from liquid petrolatum oil, paraffin oil, silicone oils, volatile or not, isoparaffins, poly-a-olefins, oils fluorinated and perfluorinated. Similarly, the waxes can be chosen from the animal, fossil, vegetable, mineral or synthetic waxes known per se. Among the organic solvents, mention may be made of lower alcohols and polyols having less than 8 carbon atoms. Thickeners other than polysaccharide alkyl ether according to the invention can be chosen in particular from crosslinked polyacrylic acids, cellulose modified or not, such as methylhydroxyethylcellulose, hydroxypropylmethylcellulose and hydroxyethylcellulose. The compositions of the invention can be prepared according to techniques well known to those skilled in the art. These compositions can be present in particular in the form of an oil, of an emulsion, simple or complex (H / E, E / H, H / E / H or E / H / E). Preferably, the compositions of the invention are in the form of an oil. When it is an emulsion, the aqueous phase thereof may comprise a non-ionic vesicular dispersion prepared according to known procedures (Bangham, Standish and Atkins, J. Mol. Biol. 13, 238 (1965), FR-2.315.991 and FR). -2,416,008).
The photostable cosmetic compositions of the invention can be used as protective compositions for the human epidermis or the hair against ultraviolet rays, as filtering compositions or also as make-up products. When the cosmetic compositions according to the invention are used for the protection of the human epidermis against UV rays or as a filter composition, they can be in the form of a suspension or dispersion in solvents or fatty substances, in the form of a non-ionic vesicular dispersion. or also in the form of an emulsion, preferably of the oil-in-water type, such as one. cream or milk, in the form of ointment, gel, solid stick, stick, spray foam or spray. When the cosmetic compositions according to the invention are used for the protection of the hair, they can be present in the form of a shampoo, lotion, gel, emulsion, non-ionic vesicular dispersion, hair spray and, for example, a composition for rinsing, for applying before or after shampooing, before or after coloring or decolorizing, before, during or after the perming or straightening, a lotion or a styling gel or traders, a lotion or a gel for marking by brush or marking, a composition of permanent or straightening, coloring or discoloration of the hair. When the compositions are used as a make-up product for the eyelashes, eyebrows or skin, such as epidermis treatment cream, foundation makeup, lipstick bar, eyelid makeup, cheek makeup, mask or profiler also called "eye-liner", they can be presented in solid or pasty, anhydrous or aqueous form, such as powders, emulsions of oil-water or water-in-oil, non-ionic vesicular dispersions or even suspensions. Concrete examples, but in no way. limiting, illustrating the invention are given below.
EXAMPLE 1
The following compositions were made (the amounts were expressed as a percentage by weight relative to the total weight of the composition). 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol 1789) 2% alcohol benzoate (C12 / C15) sold under the trade name "Finsolv TN" by Stéarineries Dubois 4% guar ethylated with a degree of substitution of approximately 2.5 x % palmitate and isopropyl csp 100%
The different compositions, according to the value of x, are indicated in the following table (I):
Table I:
The compositions were made by simple mixing of the heated constituents at about 60 ° C. For each of these compositions, the percentage of residual 4-tert-butyl-4'-methoxydibenzoylmethane was determined after irradiation by the whole UV spectrum (280-400 nm) according to the following protocol: for each composition, they were prepared four control samples and four test samples. They were deposited on unpolished PMMA (polymethyl methacrylate) plates, previously rinsed with water and then dried, 16 mg of composition which was spread over a surface of 2 to 4 cm 2. Then all the plates were left to rest for half an hour in the dark. The plates were then irradiated using the whole UV spectrum (SUNTEST CPS Heraeus) for 30 minutes, keeping the control plates in the dark during the irradiation time of the other plates. The samples were then dosed in the following manner: the filters were removed by immersing each plate in 50 g of isopropanol in order to solubilize the filters. The plates and the solvent containing the filters were then treated by ultrasound for 5 minutes to ensure efficient agitation. The residual 4-tert-butyl-4'-methoxydibenzoylmethane concentration was measured by spectrophotometry with the maximum absorption of 4-tert-butyl-4'-methoxybenzoylmethane (355 nm).
The percentage results of the residual 4-tert-butyl-4'-methoxybenzoylmethane concentration in relation to the initial 4-tert-butyl-4'-methoxydibenzoylmethane concentration are indicated in the following table (II):
Table (II)
These results clearly show that the presence of a polysaccharide alkyl ether according to the invention in a composition containing 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol 1789) significantly increases the stability of the latter within this composition.
EXAMPLE 2
A concrete example of a solar oil according to the invention is given below. The quantities are expressed by weight, in relation to the total weight of the. composition.
Solar oil:
4-tert-butyl-4'-methoxydibenzoylmethane (Parsol 1789) 1.25% α-cyano-β, β-diphenylacrylate 2-ethylhexyl sold under the trade name "Uvinul N-539" by BASF 3.75% guar ethylated with a degree of substitution of about 2.5 4% isononyl isononanoate of Stéarineries Dubois csp 100% - dyes cs perfume cs This composition was carried out by simple mixing of the heated constituents at about 60 ° C. This solar oil is particularly photostable and ensures protection in the whole range of UV radiation. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, property is claimed as contained in the following:
Claims (44)
1. A composition capable of protecting the skin and / or hair against ultraviolet radiation, of the type comprising at least one derivative of dibenzoylmethane, characterized in that it further comprises at least one polysaccharide alkyl ether formed by units including at least two different osidic rings, each unit including at least one hydroxyl group substituted by a saturated hydrocarbon alkyl chain.
2. The composition according to claim 1, characterized in that each unit includes from two to four hydroxyl groups substituted by a saturated hydrocarbon alkyl chain.
3. The composition according to claim 1 or 2, characterized in that the saturated hydrocarbon alkyl chain includes from 1 to 24 carbon atoms.
4. The composition according to claim 3, characterized in that the saturated hydrocarbon alkyl chain includes from 1 to 5 carbon atoms.
5. The composition according to claim 4, characterized in that the alkyl chain is chosen from the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl chains.
6. The composition according to any of the preceding claims, characterized in that the osidic cycles are chosen from the mannose, galactose, glucose, furanose, rhamnose, arabinose.
7. The composition according to any of the preceding claims, characterized in that the polysaccharide alkyl ether is an alkyl ether of a gum selected from guar gum, locust bean gum, karaya gum, gum trapping and their mixtures.
8. The composition according to any of the preceding claims, characterized in that the polysaccharide alkyl ether is the ethyl chain guar gum with a degree of substitution of 2 to 3.
9. The composition according to any of the preceding claims, characterized in that the polysaccharide alkyl ether has a molecular weight greater than 200,000.
10. The composition according to any of the preceding claims, characterized in that the polysaccharide alkyl ether is present in the composition with a content ranging between 0.5 and 20% by weight, relative to the total weight of the composition.
11. The composition according to claim 10, characterized in that this content ranges between 2 and 10% by weight, relative to the total weight of the composition.
12. The composition according to any of the preceding claims, characterized in that the dibenzoylmethane derivative is chosen from: - 2-methyldibenzoylmethane 4-methyldibenzoylmethane 4-isopropyldibenzoylmethane 4-tert-butyldibenzoylmethane 2,4-dimethyldibenzoylmethane - 2,5-dimethyldibenzoylmethane 4,4'-diisopropyldibenzoylmethane 4-tert-butyl-4'-methoxydibenzoylmethane 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane 2-methyl-5-tert-butyl-4 ' -methoxydibenzoylmethane - 2,4-dimethyl-4'-methoxydibenzoylmethane 2,6-dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane.
13. The composition according to claim 12, characterized in that the dibenzoylmethane derivative is 4- (tert-butyl) 4'-methoxy dibenzoyl-methane.
14. The composition according to any of the claims by the fact that the dibenzoylmethane derivative is 4-isopropyl-dibenzoylmethane.
15. The composition according to any one of the preceding claims, characterized in that the dibenzoylmethane derivative is present in the composition with a content ranging between 0.01% and 10% by weight, relative to the total weight of the composition. the composition.
16. The composition according to claim 15, characterized in that this content ranges between 0.3% and 5% by weight, relative to the total weight of the composition.
17. The composition according to any of the preceding claims, characterized in that it also comprises a cosmetically and / or dermatologically acceptable support.
18. The composition according to any of the preceding claims, characterized in that it is in the form of an oil.
19. The composition according to any of the preceding claims, characterized in that it is photostable.
20. A stabilization procedure of the. derivatives of dibenzoylmethane with respect to UV radiation, characterized in that it consists in associating with said dibenzoylmethane derivatives an effective amount of at least one polysaccharide alkyl ether formed by units that include at least two different osidic cycles, each unit including at least one group hydroxyl substituted by a saturated hydrocarbon alkyl chain.
21. The process according to claim 20, characterized in that each unit includes from two to four hydroxyl groups substituted by a saturated hydrocarbon alkyl chain.
22. The process according to claim 20 or 21, characterized in that the saturated hydrocarbon alkyl chain includes from 1 to 24 carbon atoms.
23. The process according to claim 22, characterized in that the saturated hydrocarbon alkyl chain includes from 1 to 5 carbon atoms.
24. The process according to claim 23, characterized in that the alkyl chain is chosen from the methyl, ethyl, n-propyl, -isopropyl, n-butyl, isobutyl, tert-butyl chains.
25. The process according to any of claims 20 to 24, characterized in that the osidic cycles are chosen from the mannose, galactose, glucose, furanose, rhamnose, arabinose.
26. The process according to any of claims 20 to 25, characterized in that the polysaccharide alkyl ether is an alkyl ether of a gum selected from guar gum, locust bean gum, karaya gum, gum trapping and their mixtures.
27. The process according to any of claims 20 to 26, characterized in that the polysaccharide alkyl ether is the guar chain of ethyl chain with a degree of substitution of 2 to 3.
28. The processes according to any of claims 20 to 27, characterized in that the polysaccharide alkyl ether has a molecular weight greater than 200,000.
29. The process according to any of claims 20 to 28, characterized in that the dibenzoylmethane derivative is chosen from: 2-methyldibenzoylmethane - 4-methyldibenzoylmethane 4-isopropyldibenzoylmethane 4-tert-butyldibenzoylmethane 2, 4-dimethyldibenzoylmethane 2,5-dimethyldibenzoylmethane - 4,4'-diisopropyldibenzoylmethane 4-tert-butyl-4'-methoxydibenzoylmethane 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane 2-methyl-5-tert-butyl 4'-methoxydibenzoylmethane 2,4-dimethyl-4'-methoxydibenzoylmethane - 2,6-dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane.
30. The process according to claim 29, characterized in that the dibenzoylmethane derivative is 4- (tert-butyl) 4'-methoxy dibenzoylmethane.
31. The process according to claim 29, characterized in that the dibenzoylmethane derivative is 4-isopropyl-dibenzoyl-ethane.
32. The use of a polysaccharide alkyl ether, consisting of units including at least two different osidic rings, each unit including at least one hydroxyl group substituted by a saturated hydrocarbon alkyl chain, to stabilize a dibenzoylmethane derivative with respect to UV rays content in a different composition.
33. The use according to claim 32, characterized in that each unit includes from two to four hydroxyl groups substituted by a saturated hydrocarbon alkyl chain.
34. The use according to claim 32 or 33, characterized in that the saturated hydrocarbon alkyl chain includes from 1 to 24 carbon atoms.
35. The use according to claim 34, characterized in that the saturated hydrocarbon alkyl chain includes from 1 to 5 carbon atoms.
36. The use according to claim 35, characterized in that the alkyl chain is chosen from the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl chains.
37. The composition according to any of claims 32 to 36, characterized in that the osidic cycles are chosen from mannose, galactose, glucose, furanose, rhamnose, arabinose.
38. The use according to any of claims 32 to 37, characterized in that the polysaccharide alkyl ether is an alkyl ether of a gum selected from guar gum, locust bean gum, karaya gum, gum trapping and their mixtures.
39. The use according to any of claims 32 to 38, characterized in that the polysaccharide alkyl ether is the guar chain of ethyl chain with a degree of substitution of 2 to 3.
40. The use according to any of claims 32 to 39, characterized in that the polysaccharide alkyl ether has a molecular weight greater than 200,000.
41. The use according to any of claims 32 to 40, characterized in that the dibenzoylmethane derivative is chosen from: 2-methyldibenzoylmethane 4-methyldibenzoylmethane 4-isopropyldibenzoylmethane 4-tert-butyldibenzoylmethane - 2, 4 -dimethyldibenzoylmethane 2, 5-dimethyldibenzoylmethane 4,4'-diisopropyldibenzoylmethane 4-tert-butyl-4'-methoxydibenzoylmethane 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane - 2-methyl-5-tert-butyl- 4'-methoxydibenzoylmethane 2, 4-dimethyl-4'-methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane.
42. The use according to claim 41, characterized in that the dibenzoylmethane derivative is 4- (tert-butyl) -4'-methoxy dibenzoylmethane.
43. The use according to claim 41, characterized in that the dibenzoylmethane derivative is 4-isopropyl-dibenzoylmethane.
44. A cosmetic treatment method for the protection of the skin and / or hair against ultraviolet radiation, characterized in that it consists in applying an effective amount of a composition as defined in any one of the compositions to the skin and / or the hair. . claims 1 to 19.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR96-04361 | 1996-04-05 | ||
| FR9604361A FR2747038B1 (en) | 1996-04-05 | 1996-04-05 | PHOTOSTABLE FILTERING COMPOSITION COMPRISING A DIBENZOYLMETHANE DERIVATIVE AND A POLYSACCHARIDE ALKYLETHER AND USES THEREOF |
| FR9604361 | 1996-04-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MXPA97002479A true MXPA97002479A (en) | 1998-04-01 |
| MX9702479A MX9702479A (en) | 1998-04-30 |
Family
ID=9490995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9702479A MX9702479A (en) | 1996-04-05 | 1997-04-04 | Photostable filtering composition comprising a dibenzoylmethane derivative and a polysaccharide alkylether, and its uses. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5993788A (en) |
| EP (1) | EP0804922B1 (en) |
| JP (1) | JP2996627B2 (en) |
| KR (1) | KR100244052B1 (en) |
| CN (1) | CN1092514C (en) |
| AR (1) | AR006490A1 (en) |
| AT (1) | ATE171862T1 (en) |
| AU (1) | AU683201B1 (en) |
| BR (1) | BR9700493A (en) |
| CA (1) | CA2201959C (en) |
| DE (1) | DE69700035T2 (en) |
| DK (1) | DK0804922T3 (en) |
| ES (1) | ES2125735T3 (en) |
| FR (1) | FR2747038B1 (en) |
| HU (1) | HU220447B1 (en) |
| MX (1) | MX9702479A (en) |
| PL (1) | PL186345B1 (en) |
| RU (1) | RU2137466C1 (en) |
| ZA (1) | ZA972871B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2765799B1 (en) * | 1997-07-08 | 1999-08-27 | Oreal | GLOSSY COMPOSITION CONTAINING AROMATIC OILS THICKENED BY A POLYSACCHARIDE ALKYLETHER |
| FR2799120B1 (en) * | 1999-10-01 | 2001-11-30 | Oreal | MATERIAL COMPRISING AN ORGANIC UV-A FILTER AND METHOD FOR MOVING THE MAXIMUM ABSORPTION WAVELENGTH |
| US6444195B1 (en) | 2001-06-18 | 2002-09-03 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions containing a dibenzoylmethane derivative |
| FR2857663B1 (en) | 2003-07-17 | 2007-12-21 | Bioderma Lab | NOVEL COMPOUNDS DERIVED FROM DIBENZOYLMETHANE, USE AS PHOTOACTIVABLE SOLAR FILTERS AND COSMETIC COMPOSITIONS CONTAINING SAME |
| FR2886144B1 (en) * | 2005-05-27 | 2007-06-29 | Oreal | METHOD FOR PHOTOSTABILIZING A DIBENZOYLMETHANE DERIVATIVE WITH A MEROCYANINE SULFONE DERIVATIVE; PHOTOPROTECTIVE COSMETIC COMPOSITIONS CONTAINING THE SAME. |
| TWI440926B (en) | 2010-12-31 | 2014-06-11 | Hongda Liu | Liquid crystal display apparatus |
| WO2016096344A1 (en) * | 2014-12-15 | 2016-06-23 | Unilever Plc | Compositions for providing improved sunscreen protection |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2544180C2 (en) * | 1975-10-03 | 1984-02-23 | Merck Patent Gmbh, 6100 Darmstadt | Light protection preparations for cosmetic purposes |
| NL190101C (en) * | 1978-11-13 | 1993-11-01 | Givaudan & Cie Sa | DIBENZOYL METHANE COMPOUND AND ANTI-LIGHT PROTECTIVE PREPARATION. |
| JPS57171907A (en) * | 1981-04-15 | 1982-10-22 | Kanebo Ltd | Alcohol-containing emulsified cosmetic for make-up |
| FR2506156A1 (en) * | 1981-05-20 | 1982-11-26 | Oreal | COSMETIC COMPOSITIONS CONTAINING DIBENZOYLMETHANE HYDROXYL DERIVATIVES AND THEIR USE FOR PROTECTING THE HUMAN SKIN AGAINST ULTRAVIOLET RAYS |
| FR2526658B2 (en) * | 1981-05-20 | 1986-05-23 | Oreal | COSMETIC COMPOSITIONS CONTAINING HYDROXYLATED DIBENZOYLMETHANE DERIVATIVES AND THEIR USE FOR PROTECTING THE HUMAN EPIDERMAL AGAINST ULTRAVIOLET RAYS, NEW HYDROXYLATED DIBENZOYLMETHANE DERIVATIVES AND THEIR PREPARATION PROCESS |
| DE3302123A1 (en) * | 1983-01-22 | 1984-07-26 | Haarmann & Reimer Gmbh | NEW DIBENZOLE METHANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| LU85320A1 (en) * | 1984-04-17 | 1985-11-27 | Oreal | COSMETIC COMPOSITION CONTAINING ALOESIN AS A PROTECTIVE AGENT AGAINST SUNLIGHT AND ITS USE FOR PROTECTING SKIN AND HAIR |
| JPS62114905A (en) * | 1985-11-12 | 1987-05-26 | San Ei Chem Ind Ltd | Cosmetic |
| KR890002021A (en) * | 1987-07-01 | 1989-04-07 | 원본미기재 | Benzasecin derivatives |
| DE69020978T2 (en) * | 1989-08-07 | 1995-12-14 | Procter & Gamble | Carrier system for cosmetic preparations. |
| US5229104A (en) * | 1991-04-29 | 1993-07-20 | Richardson-Vicks Inc. | Artificial tanning compositions containing positively charged paucilamellar vesicles |
| RU2020927C1 (en) * | 1991-05-22 | 1994-10-15 | Харитонова Галина Федоровна | Cream for skin protection against sun burn |
| JP2986966B2 (en) * | 1991-06-26 | 1999-12-06 | ポーラ化成工業株式会社 | Melanin production inhibitor |
| JPH0532521A (en) * | 1991-07-25 | 1993-02-09 | Max Fuakutaa Kk | Gel-like cosmetic |
| JP3220953B2 (en) * | 1992-03-19 | 2001-10-22 | 株式会社資生堂 | Sunscreen cosmetics |
| JPH0834719A (en) * | 1994-07-26 | 1996-02-06 | Kao Corp | Cosmetics |
| US5618522A (en) * | 1995-01-20 | 1997-04-08 | The Procter & Gamble Company | Emulsion compositions |
| JPH08225431A (en) * | 1995-02-22 | 1996-09-03 | Shiseido Co Ltd | Perfumery composition |
| JP3461405B2 (en) * | 1995-05-12 | 2003-10-27 | 花王株式会社 | Oil-in-water emulsion cosmetic |
| JP3579778B2 (en) * | 1995-12-28 | 2004-10-20 | 株式会社コーセー | Sun care cosmetics |
| JP3549995B2 (en) * | 1996-03-12 | 2004-08-04 | 株式会社資生堂 | W / O emulsion composition and cosmetic |
-
1996
- 1996-04-05 FR FR9604361A patent/FR2747038B1/en not_active Expired - Fee Related
-
1997
- 1997-03-11 DK DK97400536T patent/DK0804922T3/en active
- 1997-03-11 EP EP97400536A patent/EP0804922B1/en not_active Expired - Lifetime
- 1997-03-11 DE DE69700035T patent/DE69700035T2/en not_active Expired - Fee Related
- 1997-03-11 ES ES97400536T patent/ES2125735T3/en not_active Expired - Lifetime
- 1997-03-11 AT AT97400536T patent/ATE171862T1/en not_active IP Right Cessation
- 1997-03-26 AU AU16553/97A patent/AU683201B1/en not_active Ceased
- 1997-04-03 BR BR9700493A patent/BR9700493A/en not_active IP Right Cessation
- 1997-04-03 JP JP9085293A patent/JP2996627B2/en not_active Expired - Fee Related
- 1997-04-03 AR ARP970101327A patent/AR006490A1/en unknown
- 1997-04-04 ZA ZA9702871A patent/ZA972871B/en unknown
- 1997-04-04 RU RU97105413/14A patent/RU2137466C1/en not_active IP Right Cessation
- 1997-04-04 MX MX9702479A patent/MX9702479A/en unknown
- 1997-04-04 CA CA002201959A patent/CA2201959C/en not_active Expired - Fee Related
- 1997-04-04 HU HU9700712A patent/HU220447B1/en not_active IP Right Cessation
- 1997-04-04 PL PL97319292A patent/PL186345B1/en not_active IP Right Cessation
- 1997-04-04 KR KR1019970012542A patent/KR100244052B1/en not_active Expired - Fee Related
- 1997-04-04 CN CN97110953A patent/CN1092514C/en not_active Expired - Fee Related
- 1997-04-07 US US08/834,981 patent/US5993788A/en not_active Expired - Fee Related
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